Candida cyclindracea

Compound 168 is a key intermediate for the synthesis of prostaglandin or prostacyclin compounds. Scheme 5-50 shows its preparation via a retro Diels-Alder reaction and subsequent treatment. Using enzyme-catalyzed acetylation, Liu et al.80 succeeded in the asymmetric synthesis of enantiomerically pure (+)/ (—)-156 and (—)-168 from the meso-Aio 164. When treated with vinyl acetate, meso-diol 164 can be selectively acetylated to give (+)-165 in the presence of Candida cyclindracea lipase (CCL). The yield for the reaction is 81%, and the enantiomeric excess of the product is 98.3%. 

Candida cyclindracea lipase circular dichroism capillary electrophoresis Cahn-Ingold-Prelog 1,5-cyclooctadiene cyclopentadienyl group m - ch I o r o pc r be n z o i c acid circularly polarized light camphorsulfonic acid chemical shift reagent... 

Haarmann Reimer (Holzminden, Germany) in collaboration with Rolf Schmid s group at the University of Stuttgart developed a process based on the resolution of racemic menthol esters, such as acetate or benzoate esters. The team employed several lipases such as Candida cyclindracea which resulted in enantio-selectivities up to 100% e.e. (Bomscheuer, 2002). 

Inure et al94 reported the enzymatic resolution of trans-10-Azido-9-acetoxy-9,10-dihydrophenanthrene 111 in gram-scale using Candida cyclindracea lipase-catalyzed enantioselective hydrolysis in phosphate buffer. The substrate 111 (the ester) was obtained in 89 % yield and 83 % ee while the product 112 (the alcohol) was obtained in 90 % yield and 98 % ee. 

Alternatively, the enzyme may be used in an encapsulated form. Chen and Chang (1993) showed that hydrolysis of milk fat by lipase from Candida cyclindracea encapsulated in reverse micelles formed by soybean lecithin in isooctane, could be manipulated to favor the release of short-chain fatty acids by using a higher concentration of enzyme and a higher ratio of water to surfactant concentration at 45°C. 

The simple furan alcohol 131 is successfully resolved32 with a lipase from Candida cyclindracea and you should note that the same enzyme is used to form the octanoate 132 and, under different conditions, to hydrolyse it to the pure alcohol (+)-(R)-131. 

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